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Type: Artigo de Periódico
Title: Lupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth
Authors: Aline Teixeira Maciel e Silva
Cássia Gonçalves Magalhães
Lucienir Pains Duarte
Wagner da Nova Mussel
Ana Lúcia Tasca Gois Ruiz
Larissa Shiozawa
João Ernesto de Carvalho
Izabel Cristina Trindade
Sidney Augusto Vieira Filho
Abstract: The triterpene lupeol (1) and some of its esters are secondary metabolites produced by species of Celastraceae family, which have being associated with cytotoxic activity. We report herein the isolation of 1, the semi-synthesis of eight lupeol esters and the evaluation of their in vitro activity against nine strains of cancer cells. The reaction of carboxylic acids with 1 and DIC/DMAP was used to obtain lupeol stearate (2), lupeol palmitate (3) lupeol miristate (4), and the new esters lupeol laurate (5), lupeol caprate (6), lupeol caprilate (7), lupeol caproate (8) and lupeol 3’,4’-dimethoxybenzoate (9), with high yields. Compounds 1-9 were identified using FT-IR, ¹H, ¹³C-NMR, CHN analysis and XRD data and were tested in vitro for proliferation of human cancer cell activity. In these assays, lupeol was inactive (GI50> 250µg/mL) while lupeol esters 2 -4 and 7 - 9 showed a cytostatic effect. The XRD method was a suitable tool to determine the structure of lupeol and its esters in solid state. Compound 3 showed a selective growth inhibition effect on erythromyeloblastoid leukemia (K-562) cells in a concentration-dependent way. Lupeol esters 4 and 9 showed a selective cytostatic effect with low GI50 values representing promising prototypes for the development of new anticancer drugs.
Subject: Química analítica
Química farmacêutica
Células cancerosas - Crescimento
Células cancerosas - Proliferação
Agentes antineoplásicos
Química farmacêutica
Fourier, Espectroscopia de infravermelho por transformada de
Espectroscopia de ressonancia nuclear
Raios X - Difração
language: eng Brasil
Publisher: Universidade Federal de Minas Gerais
Publisher Initials: UFMG
metadata.dc.publisher.department: FAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS
Rights: Acesso Aberto
Issue Date: 2017
Appears in Collections:Artigo de Periódico

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